Tetra Butyl Ammonium Bromide Catalyzed Synthesis of Thiols and Thioethers

Abstract

A simple and commercially feasible route of synthesis of thiols and thioethers was developed using a simple phase transfer catalyst, i.e., Tetra Butyl Ammonium Bromide (TBAB). Sodium hydrogen sulfide (NaSH) is used as a sulfurization agent which is easily available and cost-effective. Thiols are obtained by treating alkyl or benzyl halides with sodium hydrogen sulfide (NaSH) in the presence of a phase transfer catalyst (TBAB) at 10 to 15℃. Thioethers are obtained by benzyl thiols treated with corresponding benzyl halides in the presence of a phase transfer catalyst (TBAB) at 10 to 15℃. Synthesis of thiols and thioethers is achieved by substitution reaction of benzyl or alkyl halides with sulfide in the presence of phase transfer catalyst (TBAB) and monochlorobenzene as a solvent at 10 to 15℃. Milder reaction conditions, excellent yield, shorter reaction time and operational simplicity are the key features of this procedure.